(2R,4aS,5R,7R,8aS)-3-methyl-8-methylidene-5-propan-2-yl-1,2,4a,5,6,7-hexahydronaphthalene-2,7,8a-triol

Details

• Internal ID: 9ed00b8f-8a71-46d3-a6c9-cd853e9ce432
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (2R,4aS,5R,7R,8aS)-3-methyl-8-methylidene-5-propan-2-yl-1,2,4a,5,6,7-hexahydronaphthalene-2,7,8a-triol
• SMILES (Canonical): CC1=CC2C(CC(C(=C)C2(CC1O)O)O)C(C)C
• SMILES (Isomeric): CC1=C[C@@H]2[C@H](C[C@H](C(=C)[C@@]2(C[C@H]1O)O)O)C(C)C
• InChI: InChI=1S/C15H24O3/c1-8(2)11-6-13(16)10(4)15(18)7-14(17)9(3)5-12(11)15/h5,8,11-14,16-18H,4,6-7H2,1-3H3/t11-,12-,13-,14-,15-/m1/s1
• InChI Key: WXNQMZLZSJGARZ-KJWHEZOQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.35 g/mol
• Exact Mass: 252.17254462 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.64
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9927	99.27%
Caco-2	-	0.7101	71.01%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.5696	56.96%
OATP2B1 inhibitior	-	0.8531	85.31%
OATP1B1 inhibitior	+	0.9237	92.37%
OATP1B3 inhibitior	+	0.9354	93.54%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9724	97.24%
P-glycoprotein inhibitior	-	0.9499	94.99%
P-glycoprotein substrate	-	0.6697	66.97%
CYP3A4 substrate	+	0.5064	50.64%
CYP2C9 substrate	-	0.7574	75.74%
CYP2D6 substrate	-	0.7094	70.94%
CYP3A4 inhibition	-	0.7679	76.79%
CYP2C9 inhibition	-	0.8085	80.85%
CYP2C19 inhibition	-	0.5789	57.89%
CYP2D6 inhibition	-	0.8985	89.85%
CYP1A2 inhibition	-	0.8318	83.18%
CYP2C8 inhibition	-	0.9546	95.46%
CYP inhibitory promiscuity	-	0.5549	55.49%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6051	60.51%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.8840	88.40%
Skin irritation	-	0.5665	56.65%
Skin corrosion	-	0.8902	89.02%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6320	63.20%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.5995	59.95%
skin sensitisation	+	0.5244	52.44%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7097	70.97%
Acute Oral Toxicity (c)	I	0.4135	41.35%
Estrogen receptor binding	-	0.7322	73.22%
Androgen receptor binding	-	0.6429	64.29%
Thyroid receptor binding	-	0.5363	53.63%
Glucocorticoid receptor binding	-	0.4725	47.25%
Aromatase binding	-	0.6904	69.04%
PPAR gamma	-	0.6916	69.16%
Honey bee toxicity	-	0.8125	81.25%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9701	97.01%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.11%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.61%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.37%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	86.25%	90.17%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.21%	96.61%
CHEMBL1937	Q92769	Histone deacetylase 2	83.68%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.30%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.94%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.69%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.41%	95.89%

Plants that contains it

• Helichrysum dasyanthum

Cross-Links

• PubChem: 162943169
• LOTUS: LTS0009708
• wikiData: Q105314780